Trifluoroacetic acid → 5-(4-bromo-naphthalen-1-yl)-2-pyrrolidin-2-yl-1H-imidazole

HRID 79776Notes

Reaction equation

HRID 79776 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]1[NH:14][C:15]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]([Br:28])=[CH:20][CH:19]=2)=[CH:16][N:17]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Br:28][C:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:18]([C:15]2[NH:14][C:13]([CH:9]3[CH2:10][CH2:11][CH2:12][NH:8]3)=[N:17][CH:16]=2)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 666204542-[5-(4-Bromo-naphthalen-1-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 666201165-(4-bromo-naphthalen-1-yl)-2-pyrrolidin-2-yl-1H-imidazoleYield 121.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[5-(4-Bromo-naphthalen-1-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester (1.00 g) was dissolved in DCM (12 mL), and trifluoroacetic acid (4 mL) was added. The reaction mixture was stirred at ambient temperature for 3 hours and evaporated under vacuum. Solid was dissolved in DCM (10 mL) and extracted with saturated NaHCO3 solution (30 mL). A solid was collected by vacuum filtration, washed with DCM, and dried under vacuum, giving 5-(4-bromo-naphthalen-1-yl)-2-pyrrolidin-2-yl-1H-imidazole (0.940 g, crude) as an off-white solid.

Workup

  1. customevaporated under vacuum
  2. dissolutionSolid was dissolved in DCM (10 mL)
  3. extractionextracted with saturated NaHCO3 solution (30 mL)
  4. filtrationA solid was collected by vacuum filtration
  5. washwashed with DCM
  6. customdried under vacuum

Sources & evidence

ORD record
ord-86cfe8d7fadb46219272c5f3d42cbedc
Source dataset
uspto-grants-2014_09
Patent number
US08841278B2

Reaction notes

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